Photopolymerization initiator and producing method thereof, polymerizable composition, ink jet recording method, and acylphosphine oxide compound

Patent metadata

Field	Value
Publication number	US-11898046-B2
Application number	US-202117159410-A
Country	US
Kind code	B2
Filing date	Jan 27, 2021
Priority date	Nov 20, 2015
Publication date	Feb 13, 2024
Grant date	Feb 13, 2024

Abstract

A photopolymerization initiator which is a compound having a structure in which one or more carbonyl groups that link to a carbon atom are further directly bonded to an aromatic ring of an aromatic acyl group that bonds to a phosphorus atom in an acylphosphine oxide structure. A producing method of a photopolymerization initiator produces the photopolymerization initiator. In a polymerizable composition and an ink jet recording method, the photopolymerization initiator is used. Furthermore, an acylphosphine oxide compound has a partial structure represented by Formula 1 or Formula 2.

First claim

What is claimed is:

1. A photopolymerization initiator which is an acylphosphine oxide compound having a structure in which one or more carbonyl groups that link to a carbon atom are further directly bonded to an aromatic ring of an aromatic acyl group that bonds to a phosphorus atom in an acylphosphine oxide structure,
wherein the carbon atom that links to the carbonyl group is an aliphatic carbon atom,
wherein the photopolymerization initiator has a constitutional unit represented by Formula 1A, Formula 2A, or Formula 2B:

wherein, in Formula 1A, Formula 2A, or Formula 2B, L's each independently represent a single bond, R P 's each independently represent a hydrogen atom or an alkyl group, R 1A 's each independently represent a monovalent hydrocarbon group in which a part of a hydrocarbon chain may be substituted with a carbonyl group, an ester bond, an amide bond, an oxygen atom, NR, and/or a sulfur atom, and R 1A is a group that links at an aliphatic carbon atom to the carbonyl group in Formula 2A, R 1B represents a divalent hydrocarbon group in which a part of a hydrocarbon chain may be substituted with a carbonyl group, an ester bond, an amide bond, an oxygen atom, NR, and/or a sulfur atom, and R 1B is a group that links at an aliphatic carbon atom to the carbonyl group in Formula 2B, R represents a hydrogen atom, an alkyl group, or an aryl group, R 2 to R 4 each independently represent an alkyl group, an aryl group, or an alkoxy group, m1 represents 3, m2 represents an integer of 0 to 5, and p represents an integer of 0 to 3.

2. The photopolymerization initiator according to claim 1 , wherein Formula 1A is Formula 1C, and Formula 2A is Formula 2C:

wherein, in Formula 1C and Formula 2C, R P 's each independently represent a hydrogen atom or a methyl group, R 1A 's each independently represent a monovalent hydrocarbon group in which a part of a hydrocarbon chain may be substituted with a carbonyl group, an ester bond, an amide bond, an oxygen atom, NR, and/or a sulfur atom, R represents a hydrogen atom, an alkyl group, or an aryl group, R 2 to R 4 each independently represent an alkyl group, an aryl group, or an alkoxy group, m1 represents 3, m2 represents an integer of 0 to 5, and p represents an integer of 0 to 3.

3. The photopolymerization initiator according to claim 1 which has two or more acylphosphine oxide structures in a molecule.

4. The photopolymerization initiator according to claim 3 ,
wherein a linking group that links two or more of the acylphosphine oxide structures together does not have any of an amino bond, a thioether bond, and a halogen atom.

5. The photopolymerization initiator according to claim 1 ,
wherein a molecular weight or a weight-average molecular weight is 300 or more and 10,000 or less.

6. A polymerizable composition comprising:
the photopolymerization initiator according to claim 1 ; and
a polymerizable compound.

7. An inkjet recording method comprising:
a step of jetting the polymerizable composition according to claim 6 onto a recording medium using an ink jet method; and
a step of curing the polymerizable composition by irradiating the jetted polymerizable composition with active radiation.

8. A producing method of the photopolymerization initiator according to claim 1 , the method comprising:
a step of reacting an acylphosphine oxide compound having one or more aromatic acyl groups that bond to a phosphorus atom with an acid halide or an acid anhydride in the presence of a Lewis acid.

Assignees

• Fujifilm Corp

Inventors

• Tsuyama Hiroaki
• Yokoi Kazuhiro
• Nakamura Kouki
• Araki Kenjiro

Classifications

• C09D11/38 Primary

  characterised by non-macromolecular additives other than solvents, pigments or dyes · CPC title

• B41M5/00

  Duplicating or marking methods; Sheet materials for use therein (by using light-sensitive materials G03; electrography, magnetography G03G {; repeatedly usable boards or tablets for writing or drawing B43L1/00}) · CPC title

• B41M7/0081

  using electromagnetic radiation or waves, e.g. ultraviolet radiation, electron beams · CPC title

• C07F9/53

  Organo-phosphine oxides; Organo-phosphine thioxides · CPC title

• C07F9/5337 Primary

  Phosphine oxides or thioxides containing the structure -C(=X)-P(=X) or NC-P(=X) (X = O, S, Se) · CPC title